PE20121280A1 - (TIO) MORPHOLINE DERIVATIVES AS S1P MODULATORS - Google Patents

(TIO) MORPHOLINE DERIVATIVES AS S1P MODULATORS

Info

Publication number
PE20121280A1
PE20121280A1 PE2012000276A PE2012000276A PE20121280A1 PE 20121280 A1 PE20121280 A1 PE 20121280A1 PE 2012000276 A PE2012000276 A PE 2012000276A PE 2012000276 A PE2012000276 A PE 2012000276A PE 20121280 A1 PE20121280 A1 PE 20121280A1
Authority
PE
Peru
Prior art keywords
alkyl
morpholin
phenyl
propionic acid
modulators
Prior art date
Application number
PE2012000276A
Other languages
Spanish (es)
Inventor
Bakker Wouter I Iwema
Hein K A C Coolen
Harmen Mons
Axel Stoit
Erick Ronken
Der Kam Elizabeth Van
Jurjen Frankena
Eric Ronken
Original Assignee
Abbvie Bahamas Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Abbvie Bahamas Ltd filed Critical Abbvie Bahamas Ltd
Publication of PE20121280A1 publication Critical patent/PE20121280A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/6533—Six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

SE REFIERE A COMPUESTOS DERIVADOS DE (TIO)MORFOLINA DE FORMULA (I) DONDE R1 ES CN, ALQUINILO(C2-C4), ALQUILO(C1-C4), CICLOALQUILO(C3-C6), ENTRE OTROS; R2 ES H, HALOGENO, ALQUILO(C1-C4) O ALCOXI(C1-C4) OPCIONALMENTE SUSTITUIDOS CON FLUOR; R3 ES ALQUILENO(C1-C4)-R5, CICLOALQUILENO(C3-C6)-R5 O -CO-CH2-R5, EN DONDE R5 ES -OH, -PO3H2, -OPO3H2, -COOH, ENTRE OTROS; R4 ES H O ALQUILO(C1-C4); R6 ES H, ALQUILO(C1-C4) O OXO; A ES -CO-O-, -O-CO-, -NH-CO-, -C=C-, ENTRE OTROS; EL ANILLO B ES FENILENO O PUEDE CONTENER UN ATOMO DE N; W ES -O-, -S-, -SO- O -SO2-. SON COMPUESTOS PREFERIDOS: ACIDO 3-{2-[4-(BENCILOXI)-FENIL]-MORFOLIN-4-IL}-PROPIONICO; ACIDO 3-{2-[4-(6-METIL-IMIDAZO[1,2-a]PIRIDIN-2-ILMETOXI)-FENIL]-MORFOLIN-4-IL}-PROPIONICO; ACIDO 3-[2-(4-FENILCARBAMOILMETOXI-FENIL)-MORFOLIN-4-IL]-PROPIONICO; ENTRE OTROS. TAMBIEN SE REFIERE A UNA COMPOSICION FARMACEUTICA. DICHOS COMPUESTOS SON MODULADORES DEL RECEPTOR ESFINGOSIN-1-FOSFATO (S1P) SIENDO UTILES EN EL TRATAMIENTO DE LA ENFERMEDAD DE ALZHEIMER, DEMENCIAREFERS TO COMPOUNDS DERIVED FROM (TIO) MORPHOLIN OF FORMULA (I) WHERE R1 IS CN, ALKYL (C2-C4), ALKYL (C1-C4), CYCLOALKYL (C3-C6), AMONG OTHERS; R2 IS H, HALOGEN, ALKYL (C1-C4) OR ALCOXY (C1-C4) OPTIONALLY SUBSTITUTED WITH FLUORINE; R3 IS ALKYLENE (C1-C4) -R5, CYCLOALKYLENE (C3-C6) -R5 OR -CO-CH2-R5, WHERE R5 IS -OH, -PO3H2, -OPO3H2, -COOH, AMONG OTHERS; R4 IS HO (C1-C4) ALKYL; R6 IS H, (C1-C4) ALKYL OR OXO; A IS -CO-O-, -O-CO-, -NH-CO-, -C = C-, AMONG OTHERS; RING B IS PHENYLENE OR MAY CONTAIN AN ATOM OF N; W IS -O-, -S-, -SO- OR -SO2-. THE PREFERRED COMPOUNDS ARE: 3- {2- [4- (BENZYLOXY) -PHENYL] -MORPHOLIN-4-IL} -PROPIONIC ACID; 3- {2- [4- (6-METHYL-IMIDAZO [1,2-a] PYRIDIN-2-ILMETOXY) -PHENYL] -MORFOLIN-4-IL} -PROPIONIC ACID; 3- [2- (4-PHENYLCARBAMOYLMETOXY-PHENYL) -MORPHOLIN-4-IL] -PROPIONIC ACID; AMONG OTHERS. IT ALSO REFERS TO A PHARMACEUTICAL COMPOSITION. SUCH COMPOUNDS ARE MODULATORS OF THE SPHINGOSIN-1-PHOSPHATE (S1P) RECEPTOR, BEING USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE, DEMENTIA

PE2012000276A 2009-08-31 2010-08-27 (TIO) MORPHOLINE DERIVATIVES AS S1P MODULATORS PE20121280A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US23851809P 2009-08-31 2009-08-31
EP09169075 2009-08-31

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PE20121280A1 true PE20121280A1 (en) 2012-10-05

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US (2) US9045441B2 (en)
EP (1) EP2473490B1 (en)
JP (1) JP5933436B2 (en)
KR (1) KR101767882B1 (en)
CN (1) CN102548976B (en)
AR (1) AR077969A1 (en)
AU (1) AU2010288477B8 (en)
CA (1) CA2772169C (en)
CR (1) CR20120153A (en)
DO (1) DOP2012000053A (en)
EC (1) ECSP12011695A (en)
ES (1) ES2452550T3 (en)
HK (1) HK1172620A1 (en)
IL (1) IL218208A (en)
MX (1) MX2012002534A (en)
NZ (1) NZ598300A (en)
PE (1) PE20121280A1 (en)
PL (1) PL2473490T3 (en)
RU (1) RU2557233C2 (en)
SG (1) SG178902A1 (en)
TW (1) TW201113263A (en)
UA (1) UA106994C2 (en)
UY (1) UY32858A (en)
WO (1) WO2011023795A1 (en)
ZA (1) ZA201201446B (en)

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Publication number Publication date
US9273017B2 (en) 2016-03-01
JP5933436B2 (en) 2016-06-08
MX2012002534A (en) 2012-04-11
AU2010288477B8 (en) 2015-09-17
KR20120092103A (en) 2012-08-20
IL218208A (en) 2016-02-29
CN102548976B (en) 2015-09-09
CR20120153A (en) 2012-05-28
HK1172620A1 (en) 2013-04-26
US20150239857A1 (en) 2015-08-27
NZ598300A (en) 2013-10-25
KR101767882B1 (en) 2017-08-14
JP2013503141A (en) 2013-01-31
TW201113263A (en) 2011-04-16
AU2010288477B2 (en) 2015-05-14
CA2772169A1 (en) 2011-03-03
DOP2012000053A (en) 2012-08-31
US20120220552A1 (en) 2012-08-30
RU2557233C2 (en) 2015-07-20
US9045441B2 (en) 2015-06-02
EP2473490B1 (en) 2014-02-26
CN102548976A (en) 2012-07-04
UY32858A (en) 2011-03-31
AU2010288477A1 (en) 2012-03-29
RU2012112477A (en) 2013-10-10
CA2772169C (en) 2017-07-18
EP2473490A1 (en) 2012-07-11
AR077969A1 (en) 2011-10-05
ECSP12011695A (en) 2012-03-30
UA106994C2 (en) 2014-11-10
PL2473490T3 (en) 2014-07-31
IL218208A0 (en) 2012-04-30
ES2452550T3 (en) 2014-04-01
ZA201201446B (en) 2014-08-27
SG178902A1 (en) 2012-04-27
WO2011023795A1 (en) 2011-03-03

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